- Interaction of a Vinylic Organosol Used as Can Coating with Solvents and Food Simulants
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Metal cans are often protected from corrosion by vinylic organosol coatings, made from PVC and epoxyphenolic (EP) resins. Using electron spin resonance, BADGE, a monomer of EP, was shown to plasticize PVC. Optimization of extraction allowed extraction of 4 mg of BADGE/dm2, so vinylic organosols appear to be worst-case coatings. Comparison of behavior between BADGE and a paramagnetic probe revealed that these compounds were trapped to a large extent in the cross-linked EP network and could not migrate at 40 °C. Contact with triglycerides, which plasticize the coating, induced high migration of BADGE. Neither isooctane nor ethanol could mimic fats, in contrast to isooctane/tert-butyl acetate mixtures. In aqueous foodstuffs, BADGE hydrolyzed into a monoepoxide and then into a bisdiol. The total amount of toxicologically relevant epoxides over shelf life was shown to reach a maximum value within 3 weeks at 40 °C, at very low levels, whatever the aqueous food simulant. After sterilization at 120 °C (20 min), the level of BADGE in the migrate is very low, whereas up to 2 mg of hydrolysis products is found in the liquid/dm2. During further storage at 40 °C, the amount of epoxides rapidly decreases.
- Cottier,Feigenbaum,Mortreuil,Reynier,Dole,Riquet
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Read Online
- METHODS OF MAKING VINYL ESTER RESINS AND STARTING MATERIALS FOR THE SAME
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Various embodiments of the present invention relate to methods of making bis(hydroxyhydrocarbyl)ethers of bisphenols and vinyl ester resins. In various embodiments, the present invention provides a method for producing a vinyl ester resin (VER). The method can include a bisphenol or a bis(hydroxy((C1-C10)hydrocarbyl)ether of the bisphenol with a vinyl ester to form the VER.
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Paragraph 0068; 0069; 0070; 0071
(2017/07/14)
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- A PROPYL-PHENYL-ETHER DERIVATIVE, AND MELANOGENESIS INHIBITOR, SKIN-LIGHTENING AGENT, ANTIMICROBIAL AGENT AND COSMETIC CONTAINING SAID PROPYL-PHENYL-ETHER DERIVATIVE
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Provided is a compound that exhibits an excellent melanogenesis-inhibiting effect (skin-lightening effect), exhibits an excellent antimicrobial effect, excels in terms of temporal stability and the like, and is suitable for use as an ingredient of a cosmetic. Said compound is a propyl-phenyl-ether derivative compound comprising a propyl group that has a substituent such as a hydroxyl group and is bound to the hydroxyl group of a phenol group that has a substituent such as a tert-butyl group. A melanogenesis inhibitor, skin-lightening agent, and antimicrobial agent containing the aforementioned compound as an active ingredient are also provided, as is a cosmetic characterized by containing said compound.
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Paragraph 0316-0319
(2016/12/12)
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- Process for manufacturing an alpha-dihydroxy derivative and epoxy resins prepared therefrom
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A process for manufacturing an α-dihydroxy derivative from an aryl allyl ether wherein such α-dihydroxy derivative can be used to prepare an α-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an α-halohydrin intermediate produced from a halide substitution of an α-dihydroxy derivative which has been obtained by a dihydroxylation reaction of an aryl allyl ether in the presence of an oxidant or in the presence of an oxidant and a catalyst.
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Page/Page column 37-38
(2008/06/13)
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- Dermal penetration and metabolism of five glycidyl ethers in human, rat and mouse skin
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1. Glycidyl ethers (GE), an important class of industrial chemicals, are considered to be potentially mutagenic in vivo because some GE have been shown to be direct mutagens in short-term in vitro tests. 2. The percutaneous penetration and metabolism of representatives of different classes of GE was studied in the fresh, full-thickness C3H mouse, and dermatomed human and Fisher 344 rat skin to determine th apparent permeability constants, lag times and metabolic profiles. 3. Five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabelled analogues were synthesized with a 14C-label using [U-14C]-epichlorohydrin. 4. There was a large variation (four orders of magnitude) in percutaneous penetration between the five GE. In general, penetration through full-thickness mouse skin was higher than through dermatomed rat skin, whereas dermatomed human skin was the least permeable. The permeability increased in the order YX4000 12GE 12GE and o-CGE penetrated the skin unchanged. For o-CGE, but none of the other GE, the percentage of the applied dose that penetrated the skin unchanged increased over time. 7. The large variation in response observed with the five selected GE indicates that GE should not be considered as a single class of compounds but rather on the basis of their individual properties.
- Boogaard,Denneman,Van Sittert
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p. 469 - 483
(2007/10/03)
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- Metabolic inactivation of five glycidyl ethers in lung and liver of humans, rats and mice in vitro
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1. Some glycidyl ethers (GE) have been shown to be direct mutagens in short-term in vitro tests and consequently GE are considered to be potentially mutagenic in vivo. However, GE may be metabolically inactivated in the body by two different enzymatic routes: conjugation of the epoxide moiety with the endogenous tripeptide glutathione (GSH) catalysed by glutathione S-transferase (GST) or hydrolysis of the epoxide moiety catalysed by epoxide hydrolase (EH). 2. The metabolic inactivation of five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), has been studied in subcellular fractions of human, C3H mouse and F344 rat liver and lung. 3. All GE were chemically very stable and resistant to aqueous hydrolysis, but were rapidly hydrolysed by EH in cytosolic and microsomal fractions of liver and lung. The aromatic GE were very good substrates for EH. In general, microsomal EH is more efficient than cytosolic EH in hydrolysis of GE, and human microsomes are more efficient than rodent microsomes. 4. The more water-soluble GE, o-CGE and HDDGE, were good substrates for GST whereas the more lipophilic GE, YX4000 and C12GE, were poor substrates for GST. In general, rodents are more efficient in GSH conjugation of GE than humans. 5. In general, the epoxide groups of YX4000 are the most and those of HDDGE the least efficiently inactivated of the five GE under study. For the other three GE no general trend was observed: the relative efficiency of inactivation varied with organ and species. 6. The large variation in metabolism observed with five representative GE indicate that GE have variable individual properties and should not be considered as a single, homogenous class of compounds.
- Boogaard,De Kloe,Bierau,Kuiken,Borkulo,VanSittert
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p. 485 - 502
(2007/10/03)
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- Reactions of 4-Chloromethyl-1,3-dioxolan-2-one with Phenols as a New Route to Polyols and Cyclic Carbonates
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Reaction of 4-chloromethyl-1,3-dioxolan-2-one (1) with phenol in the presence of potassium carbonate was studied and found to yield 4-phenoxymethyl-1,3-dioxolan-2-one (2) and 3-phenoxypropan-1,2-diol (3).The latter compound 3 was also found to be formed as the main product in the reaction of 1, phenol and sodium hydroxide at a temperature higher than 90 deg C.The effect of various factors on the reaction course and the yield of 2 and 3 was examined.It was found that the reaction studied can be extended to those of difunctional phenols such as 2,2-di(4-hydroxyphenyl) -propane producing the corresponding tetrahydroxyderivative - 2,2-bis-propane.
- Rokicki, G.,Pawlicki, J.,Kuran, W.
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p. 718 - 722
(2007/10/02)
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